2-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromide → 2-[2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]-6-diphenylmethyl-3(2H)-pyridazinone

HRID 344041Notes

Reaction equation

HRID 344041 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH3:27][O:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH2:31][CH2:32][CH2:33][CH:34]2[CH2:39][CH2:40]Br>CN(C)C=O>[CH3:27][O:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH2:31][CH2:32][CH2:33][CH:34]2[CH2:39][CH2:40][N:12]1[C:11](=[O:14])[CH:10]=[CH:9][C:8]([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:13]1

Participants

5

Reactant 3

HCID 105638762-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromideHCID 23665647Potassium tert-butoxideHCID 543237696-diphenylmethyl-3(2H)-pyridazinone

Product 1

HCID 701861902-[2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]-6-diphenylmethyl-3(2H)-pyridazinoneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-diphenylmethyl-3(2H)-pyridazinone (0.22 g) and potassium tert-butoxide (0.10 g) in N,N-dimethylformamide (2 ml) was added a solution of 2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromide (0.18 g) in N,N-dimethylformamide (3 ml) at room temperature. The reactIon mixture was stirred for 2 hours at the same temperature and partitioned between water and ethyl acetate. The organic layer was washed with water (3 times) and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane - ethyl acetate) over silica gel to afford 2-[2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.25 g) as an oil.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with water (3 times) and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (n-hexane - ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-4ae3722097b746ffbd50f2f47a61e9a9
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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